FR2586248A1 - INSECTICIDE BASED ON TRIHALOGENO-IMIDAZOLE - Google Patents

Abstract

THE PRESENT INVENTION CONCERNS A TRIHALOGENO-IMIDAZONE DERIVATIVE REPRESENTED BY THE FORMULA: (CF DRAWING IN BOPI) IN WHICH X AND Y, WHICH MAY BE THE SAME OR DIFFERENT, EACH REPRESENT A HALOGEN ATOM AND N REPRESENTS A WHOLE NUMBER OF 4 A 6, ITS PREPARATION AND AN INSECTICIDE COMPOSITION WHICH CONTAINS IT AS AN ACTIVE INGREDIENT.

Description

The present invention relates to a trihalogeno derivative

  imidazole represented by the formula (I) (hereinafter

is composed of ") X x N X N

1 X

  CH 2 O (CH 2) n Y in which X and Y, which may be the same or different, each represents a halogen atom and n represents an integer of 4 to 6, its preparation and a composition

  insecticide that contains it as an active ingredient.

  The halogen atom that represents each of the symbols X

  and Y may be a chlorine, bromine, iodine or fluorine atom.

  The authors of the invention have conducted research

  to find a compound that has insect activity

  and thus discovered that the present compound, represented by the formula (I), had excellent properties, namely that:

  1. Its insecticidal activity is very high.

  2. Its effect on cockroaches is particularly marked, with

  excellent immobilization and lethality activities.

  3. Its insecticidal effect on phyllodromia, insensitive

pyrethroids, is remarkable.

  4. Its effect in the form of fumigants is high.

  5. Its toxicity to mammals is relatively low.

  It is described in GB-A-1,316,665, US-A-3,674,874,

  etc., that a certain category of trihalogeno-

  imidazole, for example 1-n-pentyloxymethyl-2,4,5-trichloro-

  imidazole, 1-isopropoxymethyl-2,4,5-trichloroimidazole, 1- (2-bromoethyl) oxymethyl-2,4,5-tribromoimidazole, etc. can be used as an active ingredient for insecticidal compositions and / or acaricides. The present compound is within the scope of the formula given in US Pat. No. 3,674,874, but there is no reference to it in this patent. However, the authors of the invention

  discovered that, as is evident from the examples of

  described hereinafter, the present compound has insecticidal activity.

  It is extremely high in comparison with the homologues described in that patent and, in addition, has completely new insecticidal characteristics in terms of insecticidal effect on phyllodromias which are not very sensitive to pyrethroids and of effect in the form of a fumigant. The authors have thus reached the

present invention.

  The present compound can therefore be used as an active ingidient for insecticidal compositions that exhibit an effect

  on the pests in question in many places.

  In particular, it is intended to use it as an active ingredient of fumigants for the control of blattids such as

  Blattella germanica (phyllodromy), Periplaneta americana (can-

  crelat), Periplaneta fuliginosa, etc.

  Among the present compounds, those with high activity

  insecticides, in particular as insecticides for the control of cockroaches, include the following: 1- (4-Bromobutoxymethyl) -2,4,5-trichloroimidazole, 1- (4-chlorobutoxymethyl) -2,4,5-trichloroacetate; imidazole, 1- (4-bromobutoxymethyl) -2,4,5-tribromimidazole, 1- (4-chlorobutoxymethyl) -2,4,5-tribromoimidazole, 1- (6-bromohexyloxymethyl) -2,4, 5-trichloroimidazole, 1- (6-bromohexyloxymethyl) -2,4,5-tribromoimidazole, etc.

  Among these compounds, it is 1- (4-bromobutoxymethyl) -2,4,5-

  trichloro-imidazole with the highest insect activity

ticide.

  The present compounds can be prepared by reacting a trihaloimidazone represented by the formula (II)

N X

NOT

H X

  In which X represents a halogen atom, with a halomethyl ether represented by the formula (III) ZCH 2 O (CH 2) n Y (III) in which Y and Z, which may be identical or different, each represent a halogen atom; and n represents a

  whole number from 4 to 6, at a temperature of 0oC to 1500C approximately

  about 1 to 24 hours, in a solvent in the presence of a

dehydrohalogenation agent.

  The halogen atom represented by Z can be a chlorine or bromine atom, etc.

  The solvent used in this reaction may be, for example,

  an aliphatic hydrocarbon (eg hexane, hepta-

  ne, ligroine, petroleum ether), an aromatic hydrocarbon (eg benzene, toluene, xylene), a hydrocarbon

  halogen (eg chloroform, carbon tetrachloride

  bone, dichloroethane, chlorobenzene, dichlorobenzene),

  an ether (for example diethyl ether, diisopropyl ether,

  ion, dioxane, tetrahydrofuran, dimethyl ether

  ethylene glycol), ketones (eg acetone, methyl-

  ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexane

  none), esters (eg ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate), nitro compounds (eg nitroethane, nitrobenzene), nitriles (for example acetonitrile, isobutyronitrile), tertiary amines (for example pyridine, triethylamine, N, N-diethylamine, tributylamine, N-methylmorpholine),

  acid amides (for example formamide, N, N-dimethyl-

  formamide, N, N-dimethylacetamide), sulfur compounds (for example dimethylsulfoxide, sulfolane) or a mixture

of these solvents.

  The dehydrohalogenation agents include, for example, organic bases (for example pyridine, triethylamine,

  N, N-diethylaniline), inorganic bases (e.g.

  sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride), alkali metal alkoxides (e.g., sodium methoxide, sodium ethoxide) or the like.

  After completion of the reaction, the usual post-treatment

  may be applied and, if necessary, purification by

  chromatography, distillation, etc. can be done.

  Of the starting materials for the present compounds, 2,4,5-tribromoimidazole may be prepared by bromination of inidazole, for example by a process described in US Pat.

  U.S. Patent No. 3,435,050 and CH Patent No. 485,733.

  Preparation Example 1 (preparation of the present compound (1)) To a mixture of 1.03 g of 2,4,5-trichloroimidazole, 0.61 g of triethylamine and about 30 ml of toluene, 1.48 g of 4-bromobutoxymethyl bromide were added dropwise at room temperature. After stirring this mixture at room temperature for 2 hours, the deposited crystals were filtered off and washed with about 10 ml of

toluene.

  The filtrate thus obtained was concentrated under reduced pressure and the residual oily product was purified by column chromatography on silica gel to give 0.78 g.

  1- (4-bromobutoxymethyl) -2,4,5-trichloroimidazole.

n23'7 = 1.5337.

  Preparation Example 2 (preparation of the present compound (2)) To a solution of a sodium salt prepared from 0.69 g of 2,4,5-trichloroimidazole and 0.16 g of hydride of sodium-based oil at 60 Y in 5 ml of N, N-dimethylformamide,

  0.63 g of 4-chloro chloride were added dropwise.

  butoxymethyl at room temperature. After stirring at room temperature for 3 h, 50 ml of water was added to the reaction mixture, which was then run out with three portions of 3 cc of ether. The ether phase was dried over magnesium sulfate and concentrated. The oily product obtained was purified by column chromatography on silica gel,

  to give 0.83 g of 1- (4-chlorobutoxymethyl) -2,4,5-trichloroethane

imidazole. nD26'8 = 1.5140.

  Preparation Example 3 (preparation of the present compound (3)) To a solution of a sodium salt prepared from 1.22 g of 2,4,5-tribromoimidazole and 0.16 g of sodium hydride.

  60% oil-based sodium in 5 ml of N, N-dimethylformat

  In addition, 1.23 g of 4-bromobutoxymethyl bromide were added dropwise at room temperature. After stirring at room temperature for 3 h, 50 ml of water was added to the reaction mixture which was then run out with three 30 ml portions of ether. The ether phase was dried over magnesium sulfate and concentrated. The oily product obtained was purified by silica gel column chromatography,

  to give 0.74 g of 1- (4-bromobutoxymethyl) -2,4,5-tribromo-

imidazole.

n21'7 = 1.5797.

  Some of the present compounds that can be prepared

  by the process described above are indicated in the

table 1.

Table 1

  Trihalogenoimidazone derivatives represented by the formula

N X

  v, IX CH 2 O (CH 2) n Y Compound Structural formula Constant nO n Physical Y (1) 4 ci Br n '' 1.5337 (2) 4 Cl Cl n6'8 1.5140 (3) 4 Br Br n 1.5797 (4) 4 Br C n7.8 1.5620 (5) 5 Cl Br n94'0 1.5289 (6) 6 Cl Br n95.8 1.5248 (7) Br Br nD7 1.5667 When the present compounds are used as active ingredient for insecticidal compositions, they can be used as such, without addition of other ingredients. In general, however, they are formulated as emulsifiable concentrates, water-dispersible powders, dry powders, granules, oily sprays, aerosols, fumigants and

  children (eg mosquito coils, anti-mosquito

  electric mosquitoes porous ceramic plates, formulated

  "stick" type, "jet" type formulations, mist emitters), non-heating fumigants, toxic baits, etc., by mixing with solid carriers, liquid or gaseous vehicles, surfactants, other auxiliary products formulation, appetizers, etc. or by impregnation of bases

  such as brackets for mosquito coils, plaquets, etc.

  As indicated above, the insecticidal composition of the present invention is particularly suitable for cockroach control, so that in its application to

  For this purpose, its insecticidal effect may develop more effectively.

  by its use in the form of a fumigant. By fumigant, is meant one of the pesticide formulations that destroys pests or fungi by dispersing the active ingredients in the atmosphere, one way or another. As regards the form of such a fumigant, mention may be made, for example, of fumigants of the non-heating type (for example mothproof ribbons, insecticide ribbons, mothballs), fumigants of the combustion type (for example formulations of the "jet" type, baguette-type formulations, mosquito coils), fumigants of the exothermic reaction type (for example, products which give off heat by the addition of water or oxidation at the same time). air), electrically heated fumigants (eg platelets)

or the like.

  Examples of mothproof ribbons or insecticide ribbons are ribbons produced by impregnating paper, paper pulp, synthetic resin and the like. with a

active ingredient.

  As mothballs, there may be mentioned, for example, balls produced by hardening an active ingredient.

as such.

  As the main basis for type formulations

  "jet", for example, mixtures of a nitrate or nitro-

  and a thermal decomposition stimulating agent (e.g., salts of an alkaline earth metal or an alkali metal), mixtures of a guanidine salt and a caustic stimulating agent.

  thermal decomposition (for example, dichromates, chromosomes,

matte) or the like.

  As the main basis for type formulations

  "baguette", for example, mixtures of a common agent

  binder (e.g. ethylcellulose, nitrocellulose), a flame extinguishing agent (e.g. melamine, flour) a filler (especially diatomaceous earth) and a vehicle or the like. The mixture is kneaded, then put

in the form of a baguette.

  As the main base for a mosquito coil

  for example, a mixture of a combustible agent (for example wood powder, pyrethrum marc) E of a fixing agent (for example Tabu powder). This

  2C mixture is kneaded, then put in the form of a coil

mosquitoes.

  As the main basis for the formulation that pro-

  for example, mixtures of a heat-generating agent (for example sulphides, polysulphides or hydrosulfides of an alkali metal, their hydrated salts) with a substance catalytic (eg carbon black, activated carbon, charcoal, coke, asphalt) and a filler (eg natural fibers, synthetic fibers,

  synthetic resin) or the like.

  As the main basis for the formulation that pro-

  of the heat by the addition of water, for example

  mixtures of an organic foaming agent (for example azodicarboxylic

  bonamide, benzenesulfonyl hydrazide) and a general agent

  heat exchanger (eg calcium oxide) or the like.

  Examples of wafers are wafers formed by impregnating a porous asbestos plate, pulp, ceramic material, etc. with a dissolved active ingredient.

  in an organic solvent such as acetone.

  The aforementioned compositions contain from 0, CC1 to 95 'in

  weight of the compound compound as an active ingredient.

  The solid substrate comprises, for example, fine powders or granules of kaolin, attackulgite, bentonite, white clay, pyrophyllite, talc, diatomaceous earth, calcite, maize stems powder, nut shells, urea, ammonium sulfate, hydrated synthetic silica or the like. The liquid carrier comprises for example 1C aliphatic hydrocarbons (for example kerosene), aromatic hydrocarbons (for example benzene, toluene, xylene, methylnaphthalene), halogenated hydrocarbons

  (eg dichloroethane, trichlorethylene, tetra-

  carbon monoxide), alcohols (eg methyl alcohol)

  that ethyl alcohol, isopropyl alcohol, ethylene-

  glycol, Cellosolve), ketones (eg acetone, methyl ethyl ketone, cyclohexanone, isophorone), ethers

  (for example diethyl ether, dioxane, tetrahydro-

  furan), esters (eg ethyl acetate), ni-

  triles (eg acetonitrile, isobutyronitrile),

  acid amides (eg dimethylformamide, dimethyl

  acetamide), dimethylsulfoxide, vegetable oils (eg, soybean oil, cottonseed oil) or the like. The gaseous vehicle comprises, for example, freon gas, LPG (liquefied petroleum gas), dimethyl ether or the like. The surfactant used for emulsification, dispersion, wetting, etc. For example, anionic surfactants such as the salts of alkyl (aryl) sulphonate alkyl sulphates, dialkyl sulphosuccinates, the phosphoric desoxy salt of

  C30 polyoxyethylene - alkylarylether,

  naphthalenesulfonic acid / formalin densification, etc. and nonionic surfactants such as an alkyl ether and

  polyoxyethylene, polyoxyethylene block copolymers

  polyoxypropylene, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and the like. Auxiliary formulation products, such as fixing agents, dispersants, etc. can be for example lignosulfates, alginates, a polyvinyl alcohol, gum

  arabic, molasses, casein, gelatin, CMC (carboxy-

  methylcellulose), pine oil, agar-agar, etc. The sta-

  Such binders include, for example, alkyl phosphates, eg PAP (isopropyl acid phosphate), TCP (tricresyl phosphate), vegetable oils, epoxidized oils, the aforementioned surfactants, antioxidants (e.g. BHT, BHA), fatty acid salts (e.g. sodium oleate, calcium stearate), fatty acid esters (e.g.

  methyl oleate, methyl stearate) or the like.

  Examples of formulation are given below. The compounds of the invention are designated by the compound number shown in Table 1. The parts specified in

Examples relate to weight.

  Formulation Example 1 0.2 part of the present compound (1), 2 parts of xylene and

  97.8 parts of kerosene are mixed to give a pulverulent

oily production.

  Formulation example 2 parts of each of the present comoosés (1) to (7), 14

  parts of polyoxyethylenesyrylphenyl ether, 6 parts

  calcium dodecylbenzenesulfonate and 70 parts of

  xylene are mixed well to give an emulsified concentrate.

reliable of each compound.

Formulation example 3

  20 parts of the present compound (2), 10 parts of fenitro-

  thion, 3 parts of calcium lignosulfonate, 2 parts of

  sodium lauryl sulphate and 65 parts of syn-

  tea are well pulverized and mixed together, for

  give a dispersible powder in water.

  -C Formulation Example 4 1 part of the present compound (1), 2 parts of carbaryl, 87 kaolin darts and 10 parts of talc are well pulverized

  and mixed together to give a dry powder.

Expression of formulation 5

  7 and 5 parts of the present compound (1), 1 part of hyaline silica

  synthetic corn, 2 parts of calcium lignosulfonate,

  3C parts of bentonite and 62 parts of kaolin are well

  checked and mixed together, well kneaded with water, 1c

  granulated and then dried to give a granulated product.

Formulation example 6

  0.05 part of the present compound (1), 0.2 part of tetra-

  methrin, 0.05 part of resmethrin, 7 parts of xylene and 32.7 parts of deodorized kerosene are mixed well to form a solution. The solution is loaded into an aerosol can and, after attaching a bomb valve, 60 parts of a propellant (liquefied petroleum gas) are loaded into it.

  through the valve under pressure, to give an aerosol.

Formulation example 7

  0.3 g of the present compound (1) and 0.3 g of d-trans-chrysantane

  Allethrin themaate is dissolved in 20 ml of methanol. This solution and 99.4 g of an anti-mosquito coil stand, which is a 3: 5: 1 mixture of Tabu powder, pyrethrum marc

  and wood powder, are mixed uniformly with stirring.

  After evaporation of the methanol, 150 ml of water are added to the residue and the mixture is well kneaded, shaped and dried for

  give a mosquito coil.

  Formulation Example 8 100 mg of each of the present compounds (1) to (7) are dissolved in a suitable amount of acetone and a porous ceramic plate of 4.0 cm x 4.0 cm x 1.2 cm (thickness ) is

  impregnated with this solution to give a heating fumigant

iron of each of the compounds.

  These compositions are used as such or in the form of dilute aqueous solutions. They can also be used mixed with other insecticides, acaricides,

  nematocides, fungicides, herbicides, growth regulators

  plants, fertilizers, amendments or the like.

  3? When the present compounds are used in the form of emulsifiable concentrates or water-dispersible powders as an insecticidal composition, their concentration in the artiplication is from 10 to 10 pDm. When used in the form of dry powder, granules, oily spray or aerosol, they are applied as such, without dilution. 2nd test examples are given below. Compounds used as controls are designated by their compound symbol

in Table 2.

1 1

Table 2

  Symbol of F composed of Structural Formula Compound Name - Cl N C (n) Ci2oc 4H9 (n) C1 C <N C-C1 CH20C5H11 Br Br / N / N - Br

CH2 OCH2CH

Br N Br B Br (n) 2Br

CH2OCH2CH2C1

O

OCNHCH3

\ CH3

OCH / C

  Compound described in US Pat.

3,674,874

  Compound described in GB Patent No. 1,316,665 and US Pat.

3,674,874

  Compound described in US Pat.

3,674,874 -

  As above Propoxur ABCDE Test Example 1 1-1 Mouse Acute Oral Toxicity Test The present compounds and the control were each diluted with corn oil at the prescribed concentrations and diluted solutions were administered. strength in the stomach of ICR male mice, six weeks old and weighing 24 to 31 g, who had not been given food

  for about 20 hours at 0.1 ml / 10 g body weight.

  The mice were kept under observation for 4 h 1 C after administration, then fed with an appetite and water in a cage. The number of dead and live animals was increased by seven days of monitoring and

  a value of LD50 (lethal dose at 50% -) (5 mice per group).

  1-2 Insecticide activity test on phyllodromy Each of the compounds present and the control was diluted with

  acetone at the prescribed concentrations and applied topically

  ventral chest of adult male phyllodromy (Blat-

  tella germanica) which belonged to a strain not very sensitive to pyrethrils at the rate of 1 / ul / adult. After application, the adults were fed bait and water in a polyethylene dish. After two days, the number of dead and alive was recorded to determine the LD50

  (10 adults per group, two repeated trials).

  The results of the acute oral toxicity test in mice and the insecticidal activity test on phyllodromies,

  concerning the compounds tested, are presented in Table 3.

  It is apparent from this table that the present compounds have the characteristics that the toxicity to warm-blooded animals is low and that the insecticidal activity on insects

  harmful is high. In order to highlight these characteristics

  the following factor of safety:

  from the results of the tests.

  Coefficient Toxicity to mice (LD50, mg / kg) safety = Insecticidal activity (LD50, mg / kg)

  The calculation gave, for both of them, present

  poses (1) and (2), a safety factor of more than 50. This means that the present compounds are more than 50 times more harmless for warm-blooded animals. On the other hand, for witnesses (C), (D) and (E), respectively,

  safety factors of 16, 18 and 5.6.

Table 3

  Compound Oral toxicity Insecticidal activity Acute tested coefficient for safety phyllodromy mice: LD50 LD50 (mg / kg) (mg / kg) (a) (b) (a) / (b)

(1)? 300 6,4> 47

(2)> 3CO 6.2 48

(A) - 10

(B) - 20 -

(c) 110 7.0 16

(D) 170 9.4 18

(E) 39 7.0 5.6

Example

  Each of the present compounds and controls were diluted with acetone and topically applied to the ventral chest of male adults of Periplaneta fuliginosa at 10 μg / adult. After the application, the adults were fed with bait and water. After two days, the number of dead and alive was recorded for the determination of

  mortality rate (5 adults per group, two repeated trials).

  The results are shown in Table 4.

Table 4

Compound tested Mortality (c)

(1) 80

(2) 100

(B) 40

  Untreated 10 Test Example 3 Four polyethylene cups (inner diameter, 10 cm, height, 8 cm) coated with butter on the inner surface were respectively placed at the four corners of the bottom of a 7C glass cage: x 70 x 70cm (0.34 m3). 10 adults of phyllodrome (Blattella germanica) per group, belonging to a

  strain not susceptible to pyrethrils, were released in each

  one of two polyethylene cups and 10 female adults of the insect per group were released in each of the other two. An electric heater was placed in the middle of the bottom

  the glass cage and the porous ceramic

  compounds of the invention and controls and obtained according to the formulation example 8 (13.7 mg / plate: 40 mg / m3),

  were placed on him respectively. The plate was heated

  fairy at 2000C by passing current for 2C mn. The number of immobilized insects was recorded as a function of time to determine the TK50 (50% downtime). 80 minutes after the start of the application of current, the cups containing the test insects were extracted and the test insects were fed with water and bait. After 2 days, the number of dead and alive was recorded to determine a death rate. The results are shown in Table 5

* Table 5

  Test compound TK50 (min) Mortality (5)

(1) 28,100

(2) 41 1C0o

(3) 45,100

(4) 58 90

(5) 68 87.5

(7) 65 92.5

(B)> 80 47.5

(E)> 80 0

  Test example 4 3C At the bottom of a 183x! 85x! 83cm Peet Grady chamber (6.1

  m3), three polyethylene cups were

  laughing, 10 cm; height, 8 cm) coated with butter on the surface

  and 20 Dhyllodromia (10 males and 10 females) (Blattel-

  germanica), belonging to a strain not very sensitive to pyrethroid

  throids, were released in each dish. An electric radiator was placed in the middle of the bottom of the chamber and porous ceramic plates impregnated with the present compounds and controls, obtained according to the formulation example 8 (61 mg / plate: 10 mg / mr), were respectively placed on him. The plate was heated to about 2000C by current flow for 70 minutes. Immobilized insects were counted as a function of time to determine TK50 (immobilization time). 80 minutes after the start of the application of current, the cups containing the test insects were removed from the chamber and the test insects were fed with bait and water. After 3 days, dead and live were counted to determine a death rate. The results are

presented in Table 6.

Table 6

  Test example Two groups of 5 male adults and 5 female adults each of phyllodromia (Blattella germanica), one belonging to a pyrethroid sensitive strain and the other to a low susceptibility strain, were released into a diameter polyethylene cup, coated with a thin layer of Vaseline 3.0 on the inner surface. After being covered with a 1.19 mm nylon gauze, Lacoupelle was placed on the bottom of a

  glass cylinder (inside diameter, 10 cm, height, 37 cm).

  Afterwards, 0.6 ml of each of the 0.1% oily sprays of the present compounds and controls, prepared according to Formulation Example 1, were applied directly to the adults by means of a spray gun. a pressure Compound tested TK50 (min) Mortality (5)

(1) 38 100

(2) 63 80

(3) 77 90

(6) 41 95

(A)> 80 8

(B), 80 o (c) 7 80 40

(D)> 80 3

(E) D 80 C

  0.6 atm, from the top of the cylinder. Immobilized insects were counted as a function of time to obtain TK50 (50% immobilization time) (two repeated trials). The

  The results are shown in Table 7.

Table 7

  Tested compound TK50 of the T50 strain of the susceptible strain which is not very sensitive to (mn) pyrethroids (mn)

(1) 1.100

(3) 1,1 1,2

(4) 2.1 - 0.5

(7) 2.3 0.72

(A)> 20> 20

(B)> 20> 20

(C)> 20> 20

(D)> 20 ^ 20

(E) 6.9 10

17 2586248

Claims (14)

1, trihalogeno-imidazole derivative represented by the formula N.XXiXCH.sub.2 (CH.sub.2) nY wherein X and Y, which may be identical or different, each represent a halogen atom and n represents an integer of 4 to 6.   2. A trihalogenoimidazole derivative according to claim 1, in which n is 4.   3. 1- (4-Bromobutoxymethyl) -2,4,5-trichloroimidazole.   4. 1- (4-Chlorobutoxymethyl) -2,4,5-trichloroimidazole.   5. 1- (4-Bromobutoxymethyl) -2,4,5-tribromoimidazole.   6. 1- (4-Chlorobutoxymethyl) -2,4,5-tribromoimidazole.   7. 1- (6-Bromohexyloxymethyl) -2,4,5-trichloroimidazole.   8. 1- (6-Bromohexyloxymethyl) -2,4,5-tribromoimidazole.   9. An insecticidal composition that includes, as an   active, an amount sufficient to have an   ticide of a trihalogenoimidazole derivative represented by the formula N X N / I X N i Hx CH2O (CH2) nY 18 2586248   wherein X and Y, which may be the same or different, each represents a halogen atom and n represents a   an integer from 4 to 6, and an inert excipient.   An insecticidal composition according to claim 9 in the form of a cockroach fumigant. An insecticidal composition according to claim 10, wherein the trihalogenoimidazole derivative is a trihalogenoimidazole derivative represented by the formula X r N X CH20 (CH2) 4Y   wherein X and Y, which may be the same or different,   each represent a halogen atom.   12. Insecticidal composition according to claim 10, in   which the trihalogenoimidazole derivative is 1- (4-bromo)   butoxymethyl) -2,4,5-trichloro-imidazole. 13. Insecticidal composition according to claim 10, in   which the trihalogenoimidazole derivative is 1- (4-chloro)   butoxymethyl) -2,4,5-trichloro-imidazole. 14. Insecticidal composition according to claim 10, in   which the trihalogenoimidazole derivative is. 1- (4-bromo-   butoxymethyl) -2,4,5-tribromo-imidazole.   15. An insecticidal composition according to claim 10 in which   which the trihalogenoimidazole derivative is 1- (4-chloro)   butoxymethyl) -2,4,5-tribromo-imidazole. 16. Insecticidal composition according to claim 10, in which   which the trihalogenoimidazole derivative is 1- (6-bromine)   Hexyloxymethyl) -2,4,5-trichloro-imidazole. 17. An insecticidal composition according to claim 10 in which   which the trihalogenoimidazole derivative is 1- (6-bromine)   Hexyloxymethyl) -2,4,5-tribromo-imidazole. 18. A method of destroying insects comprising applying an amount sufficient to have an insecticidal effect of a trihalogenoimidazole derivative represented by the formula N 'X x NY I1 X   Wherein X and Y, which may be the same or different, each represents a halogen atom and n represents an integer of 4 to 6, to insects. An insect killing method according to claim 18,   in which insects are cockroaches.   20. The method of destroying insects according to claim 19, wherein the trihalogenoimidazole derivative is a trihalogenoimidazole derivative represented by the formula X X-: N X. CH2O (CH2) 4Y   in which X and Y, which may be the same or different,   each represent a halogen atom.   An insect killing method according to claim 19,   wherein the trihalogenoimidazole derivative is 1- (4-bromo)   butoxymethyl) -2,4,5-trichloro-imidazole. 22. The method of destroying insects according to claim 19,   wherein the trihalogenoimidazole derivative is 1- (4-chloro)   butoxymethyl) -2,4,5-trichloro-imidazole. An insect destruction method according to claim 19,   wherein the trihalogenoimidazole derivative is 1- (4-bromo)   butoxymethyl) -2,4,5-tribromo-imidazole. Method of destroying insects according to claim 19,   wherein the trihalogenoimidazole derivative is 1- (4-chloro)   butoxymethyl) -2,4,5-tribromo-imidazole. An insect destruction method according to claim 19,   wherein the trihalogenoimidazole derivative is 1- (6-bromine)   hexyloxymethyl) -2,5,5-trichloroimidazole.   26. A method of destroying insects according to claim 19,   wherein the trihalogenoimidazole derivative is 1- (6-bromine)   Hexyloxymethyl) -2?, 5-tribromo-imidazole.